JP2016508500A5 - - Google Patents
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- Publication number
- JP2016508500A5 JP2016508500A5 JP2015556113A JP2015556113A JP2016508500A5 JP 2016508500 A5 JP2016508500 A5 JP 2016508500A5 JP 2015556113 A JP2015556113 A JP 2015556113A JP 2015556113 A JP2015556113 A JP 2015556113A JP 2016508500 A5 JP2016508500 A5 JP 2016508500A5
- Authority
- JP
- Japan
- Prior art keywords
- benzamido
- alkyl
- pain
- halogen
- pharmaceutically acceptable
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 229910052736 halogen Inorganic materials 0.000 claims description 102
- 150000002367 halogens Chemical class 0.000 claims description 102
- 150000001875 compounds Chemical class 0.000 claims description 70
- 150000003839 salts Chemical class 0.000 claims description 45
- 208000002193 Pain Diseases 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 28
- 208000004296 neuralgia Diseases 0.000 claims description 14
- 125000002723 alicyclic group Chemical group 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 7
- 208000021722 neuropathic pain Diseases 0.000 claims description 7
- 206010028391 Musculoskeletal Pain Diseases 0.000 claims description 6
- 208000027418 Wounds and injury Diseases 0.000 claims description 6
- 208000014674 injury Diseases 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 206010065390 Inflammatory pain Diseases 0.000 claims description 5
- 230000006378 damage Effects 0.000 claims description 5
- 210000005036 nerve Anatomy 0.000 claims description 5
- -1 t- butyl Chemical group 0.000 claims description 5
- 208000005890 Neuroma Diseases 0.000 claims description 4
- 108010053752 Voltage-Gated Sodium Channels Proteins 0.000 claims description 4
- 102000016913 Voltage-Gated Sodium Channels Human genes 0.000 claims description 4
- 208000005298 acute pain Diseases 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- 229940124597 therapeutic agent Drugs 0.000 claims description 4
- 206010034620 Peripheral sensory neuropathy Diseases 0.000 claims description 3
- 206010036376 Postherpetic Neuralgia Diseases 0.000 claims description 3
- 208000010261 Small Fiber Neuropathy Diseases 0.000 claims description 3
- 206010073928 Small fibre neuropathy Diseases 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 230000000968 intestinal effect Effects 0.000 claims description 3
- 230000003349 osteoarthritic effect Effects 0.000 claims description 3
- 208000017692 primary erythermalgia Diseases 0.000 claims description 3
- 201000005572 sensory peripheral neuropathy Diseases 0.000 claims description 3
- 239000003981 vehicle Substances 0.000 claims description 3
- POHBHELIQIIUKS-UHFFFAOYSA-N 3-methyl-4-[(2-phenoxybenzoyl)amino]benzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1NC(=O)C1=CC=CC=C1OC1=CC=CC=C1 POHBHELIQIIUKS-UHFFFAOYSA-N 0.000 claims description 2
- SZKVUKWDHVSELR-UHFFFAOYSA-N 4-[(2-phenoxybenzoyl)amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC=CC=C1OC1=CC=CC=C1 SZKVUKWDHVSELR-UHFFFAOYSA-N 0.000 claims description 2
- ZYORVEKORXNUEM-UHFFFAOYSA-N 4-[[2-(4-fluoro-2-methoxyphenoxy)-4,6-bis(trifluoromethyl)benzoyl]amino]benzoic acid Chemical compound COC1=CC(F)=CC=C1OC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1C(=O)NC1=CC=C(C(O)=O)C=C1 ZYORVEKORXNUEM-UHFFFAOYSA-N 0.000 claims description 2
- CCFLCDDJGGMPDK-UHFFFAOYSA-N 4-[[2-[4-(trifluoromethoxy)phenoxy]-4-(trifluoromethyl)benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1OC1=CC=C(OC(F)(F)F)C=C1 CCFLCDDJGGMPDK-UHFFFAOYSA-N 0.000 claims description 2
- DZORGHOZKZHPLX-UHFFFAOYSA-N 4-[[4,5-dichloro-2-[4-(2,2,2-trifluoroethoxy)phenoxy]benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC(Cl)=C(Cl)C=C1OC1=CC=C(OCC(F)(F)F)C=C1 DZORGHOZKZHPLX-UHFFFAOYSA-N 0.000 claims description 2
- QPVZBOZWYRYQOY-UHFFFAOYSA-N 5-[[2-(2-chlorophenoxy)-5-(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1NC(=O)C1=CC(C(F)(F)F)=CC=C1OC1=CC=CC=C1Cl QPVZBOZWYRYQOY-UHFFFAOYSA-N 0.000 claims description 2
- IUYUKZBMJINCLE-UHFFFAOYSA-N 5-[[2-(4-fluorophenoxy)-4-(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1OC1=CC=C(F)C=C1 IUYUKZBMJINCLE-UHFFFAOYSA-N 0.000 claims description 2
- NBWXLOUGPHXUKY-UHFFFAOYSA-N 5-[[2-(4-methoxyphenoxy)-4,6-bis(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1OC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1C(=O)NC1=CC=C(C(O)=O)N=C1 NBWXLOUGPHXUKY-UHFFFAOYSA-N 0.000 claims description 2
- LFHRVAHCKMGOPT-UHFFFAOYSA-N 5-[[4,5-dichloro-2-(2,4-dimethoxyphenoxy)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound COC1=CC(OC)=CC=C1OC1=CC(Cl)=C(Cl)C=C1C(=O)NC1=CC=C(C(O)=O)N=C1 LFHRVAHCKMGOPT-UHFFFAOYSA-N 0.000 claims description 2
- CGCFKBNXDFEYIJ-UHFFFAOYSA-N 5-[[4,5-dichloro-2-[2-(difluoromethoxy)phenoxy]benzoyl]amino]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1NC(=O)C1=CC(Cl)=C(Cl)C=C1OC1=CC=CC=C1OC(F)F CGCFKBNXDFEYIJ-UHFFFAOYSA-N 0.000 claims description 2
- VJNROMFRLBVAHF-UHFFFAOYSA-N 5-chloro-2-methoxy-4-[(2-phenoxybenzoyl)amino]benzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC(NC(=O)C=2C(=CC=CC=2)OC=2C=CC=CC=2)=C1Cl VJNROMFRLBVAHF-UHFFFAOYSA-N 0.000 claims description 2
- 206010003497 Asphyxia Diseases 0.000 claims description 2
- 208000008035 Back Pain Diseases 0.000 claims description 2
- 206010058019 Cancer Pain Diseases 0.000 claims description 2
- 208000010693 Charcot-Marie-Tooth Disease Diseases 0.000 claims description 2
- 208000000094 Chronic Pain Diseases 0.000 claims description 2
- 208000011231 Crohn disease Diseases 0.000 claims description 2
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 2
- 208000001640 Fibromyalgia Diseases 0.000 claims description 2
- 206010019233 Headaches Diseases 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 206010021639 Incontinence Diseases 0.000 claims description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
- 208000005615 Interstitial Cystitis Diseases 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 208000031481 Pathologic Constriction Diseases 0.000 claims description 2
- 208000004983 Phantom Limb Diseases 0.000 claims description 2
- 206010056238 Phantom pain Diseases 0.000 claims description 2
- 208000008765 Sciatica Diseases 0.000 claims description 2
- 238000011225 antiretroviral therapy Methods 0.000 claims description 2
- 206010003119 arrhythmia Diseases 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 208000003295 carpal tunnel syndrome Diseases 0.000 claims description 2
- 238000002512 chemotherapy Methods 0.000 claims description 2
- 231100000869 headache Toxicity 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 230000036262 stenosis Effects 0.000 claims description 2
- 208000037804 stenosis Diseases 0.000 claims description 2
- 230000000472 traumatic effect Effects 0.000 claims description 2
- 206010044652 trigeminal neuralgia Diseases 0.000 claims description 2
- 208000004550 Postoperative Pain Diseases 0.000 claims 3
- ZWSJDCCDISWMKX-UHFFFAOYSA-N 4-[[2-(4-fluoro-2-methylphenoxy)-5-(trifluoromethyl)benzoyl]amino]benzoic acid Chemical compound CC1=CC(F)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC=C(C(O)=O)C=C1 ZWSJDCCDISWMKX-UHFFFAOYSA-N 0.000 claims 2
- KXJDXJMNXMKFQA-UHFFFAOYSA-N 5-[[4,5-dichloro-2-(4-fluoro-2-methoxyphenoxy)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound COC1=CC(F)=CC=C1OC1=CC(Cl)=C(Cl)C=C1C(=O)NC1=CC=C(C(O)=O)N=C1 KXJDXJMNXMKFQA-UHFFFAOYSA-N 0.000 claims 2
- IFLJQZOHWQKXBE-UHFFFAOYSA-N 3-[(2-phenoxybenzoyl)amino]benzoic acid Chemical compound O(C1=CC=CC=C1)C1=C(C(=O)NC=2C=C(C(=O)O)C=CC=2)C=CC=C1 IFLJQZOHWQKXBE-UHFFFAOYSA-N 0.000 claims 1
- MZIVXQQTMDYTAZ-UHFFFAOYSA-N 4-[[2-(2,4-difluorophenoxy)-4,6-bis(trifluoromethyl)benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C(C(=CC(=C1)C(F)(F)F)C(F)(F)F)=C1OC1=CC=C(F)C=C1F MZIVXQQTMDYTAZ-UHFFFAOYSA-N 0.000 claims 1
- LLGVNUHNAGGBMF-UHFFFAOYSA-N 4-[[2-(2,4-difluorophenoxy)-4-(1,1,2,2,2-pentafluoroethyl)benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC=C(C(F)(F)C(F)(F)F)C=C1OC1=CC=C(F)C=C1F LLGVNUHNAGGBMF-UHFFFAOYSA-N 0.000 claims 1
- MRBUJXKMAOIITA-UHFFFAOYSA-N 4-[[2-(2,4-difluorophenoxy)-4-(trifluoromethyl)benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1OC1=CC=C(F)C=C1F MRBUJXKMAOIITA-UHFFFAOYSA-N 0.000 claims 1
- BAVGXISUWOMPHG-UHFFFAOYSA-N 4-[[2-(2-chloro-4-fluorophenoxy)-4-(1,1,2,2,2-pentafluoroethyl)benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC=C(C(F)(F)C(F)(F)F)C=C1OC1=CC=C(F)C=C1Cl BAVGXISUWOMPHG-UHFFFAOYSA-N 0.000 claims 1
- CAROJXJPUIPNPU-UHFFFAOYSA-N 4-[[2-(2-chloro-4-fluorophenoxy)-4-(trifluoromethyl)benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1OC1=CC=C(F)C=C1Cl CAROJXJPUIPNPU-UHFFFAOYSA-N 0.000 claims 1
- ZDFFCDWYMIMFCV-UHFFFAOYSA-N 4-[[2-(4-fluoro-2-methoxyphenoxy)-4-(1,1,2,2,2-pentafluoroethyl)benzoyl]amino]benzoic acid Chemical compound COC1=CC(F)=CC=C1OC1=CC(C(F)(F)C(F)(F)F)=CC=C1C(=O)NC1=CC=C(C(O)=O)C=C1 ZDFFCDWYMIMFCV-UHFFFAOYSA-N 0.000 claims 1
- IZPCPMZRYGDVDG-UHFFFAOYSA-N 4-[[2-(4-fluoro-2-methylphenoxy)-4,6-bis(trifluoromethyl)benzoyl]amino]benzoic acid Chemical compound CC1=CC(F)=CC=C1OC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1C(=O)NC1=CC=C(C(O)=O)C=C1 IZPCPMZRYGDVDG-UHFFFAOYSA-N 0.000 claims 1
- AFMYVWVPIHWHLQ-UHFFFAOYSA-N 4-[[2-(4-fluoro-2-methylphenoxy)-4-(1,1,2,2,2-pentafluoroethyl)benzoyl]amino]benzoic acid Chemical compound CC1=CC(F)=CC=C1OC1=CC(C(F)(F)C(F)(F)F)=CC=C1C(=O)NC1=CC=C(C(O)=O)C=C1 AFMYVWVPIHWHLQ-UHFFFAOYSA-N 0.000 claims 1
- WHSJMGMHKHPGIL-UHFFFAOYSA-N 4-[[2-(4-fluoro-2-methylphenoxy)-4-(trifluoromethyl)benzoyl]amino]benzoic acid Chemical compound CC1=CC(F)=CC=C1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC=C(C(O)=O)C=C1 WHSJMGMHKHPGIL-UHFFFAOYSA-N 0.000 claims 1
- FOTNRCKKBGVZMV-UHFFFAOYSA-N 4-[[2-(4-fluorophenoxy)-4,6-bis(trifluoromethyl)benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C(C(=CC(=C1)C(F)(F)F)C(F)(F)F)=C1OC1=CC=C(F)C=C1 FOTNRCKKBGVZMV-UHFFFAOYSA-N 0.000 claims 1
- WHKNHAUMJCTTLG-UHFFFAOYSA-N 4-[[4,5-dichloro-2-(2,4-difluorophenoxy)benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC(Cl)=C(Cl)C=C1OC1=CC=C(F)C=C1F WHKNHAUMJCTTLG-UHFFFAOYSA-N 0.000 claims 1
- PVLVVQUGLDODSS-UHFFFAOYSA-N 4-[[4,5-dichloro-2-(2,4-dimethoxyphenoxy)benzoyl]amino]benzoic acid Chemical compound COC1=CC(OC)=CC=C1OC1=CC(Cl)=C(Cl)C=C1C(=O)NC1=CC=C(C(O)=O)C=C1 PVLVVQUGLDODSS-UHFFFAOYSA-N 0.000 claims 1
- OOZXERKWFWPVJT-UHFFFAOYSA-N 4-[[4,5-dichloro-2-(2-chloro-4-fluorophenoxy)benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC(Cl)=C(Cl)C=C1OC1=CC=C(F)C=C1Cl OOZXERKWFWPVJT-UHFFFAOYSA-N 0.000 claims 1
- ZTXIJQTYASXCNZ-UHFFFAOYSA-N 4-[[4,5-dichloro-2-(2-chloro-4-methoxyphenoxy)benzoyl]amino]benzoic acid Chemical compound ClC1=CC(OC)=CC=C1OC1=CC(Cl)=C(Cl)C=C1C(=O)NC1=CC=C(C(O)=O)C=C1 ZTXIJQTYASXCNZ-UHFFFAOYSA-N 0.000 claims 1
- LMNGTJLHWMMCFG-UHFFFAOYSA-N 4-[[4,5-dichloro-2-(2-fluoro-4-methoxyphenoxy)benzoyl]amino]benzoic acid Chemical compound FC1=CC(OC)=CC=C1OC1=CC(Cl)=C(Cl)C=C1C(=O)NC1=CC=C(C(O)=O)C=C1 LMNGTJLHWMMCFG-UHFFFAOYSA-N 0.000 claims 1
- BOWBWUKGDFJJDA-UHFFFAOYSA-N 4-[[4,5-dichloro-2-(3-fluoro-4-methoxyphenoxy)benzoyl]amino]benzoic acid Chemical compound C1=C(F)C(OC)=CC=C1OC1=CC(Cl)=C(Cl)C=C1C(=O)NC1=CC=C(C(O)=O)C=C1 BOWBWUKGDFJJDA-UHFFFAOYSA-N 0.000 claims 1
- FYSNDWMSTSNSPW-UHFFFAOYSA-N 4-[[4,5-dichloro-2-(4-chloro-2-methoxyphenoxy)benzoyl]amino]benzoic acid Chemical compound COC1=CC(Cl)=CC=C1OC1=CC(Cl)=C(Cl)C=C1C(=O)NC1=CC=C(C(O)=O)C=C1 FYSNDWMSTSNSPW-UHFFFAOYSA-N 0.000 claims 1
- ZPTZKRNZFFQAKZ-UHFFFAOYSA-N 4-[[4,5-dichloro-2-(4-chloro-2-methylphenoxy)benzoyl]amino]benzoic acid Chemical compound CC1=CC(Cl)=CC=C1OC1=CC(Cl)=C(Cl)C=C1C(=O)NC1=CC=C(C(O)=O)C=C1 ZPTZKRNZFFQAKZ-UHFFFAOYSA-N 0.000 claims 1
- JPVADBDXDGHZBJ-UHFFFAOYSA-N 4-[[4,5-dichloro-2-(4-fluoro-2-methoxyphenoxy)benzoyl]amino]benzoic acid Chemical compound COC1=CC(F)=CC=C1OC1=CC(Cl)=C(Cl)C=C1C(=O)NC1=CC=C(C(O)=O)C=C1 JPVADBDXDGHZBJ-UHFFFAOYSA-N 0.000 claims 1
- OFOIUNYHRNAMCV-UHFFFAOYSA-N 4-[[4,5-dichloro-2-(4-fluoro-2-methylphenoxy)benzoyl]amino]benzoic acid Chemical compound CC1=CC(F)=CC=C1OC1=CC(Cl)=C(Cl)C=C1C(=O)NC1=CC=C(C(O)=O)C=C1 OFOIUNYHRNAMCV-UHFFFAOYSA-N 0.000 claims 1
- MECYBMKMICVTAK-UHFFFAOYSA-N 4-[[4,5-dichloro-2-(4-fluorophenoxy)benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC(Cl)=C(Cl)C=C1OC1=CC=C(F)C=C1 MECYBMKMICVTAK-UHFFFAOYSA-N 0.000 claims 1
- TWHKITDGPNXHCU-UHFFFAOYSA-N 4-[[4,5-dichloro-2-[2-(difluoromethoxy)phenoxy]benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC(Cl)=C(Cl)C=C1OC1=CC=CC=C1OC(F)F TWHKITDGPNXHCU-UHFFFAOYSA-N 0.000 claims 1
- NJFDHBSKHZPRIL-UHFFFAOYSA-N 4-[[4,5-dichloro-2-[4-(trifluoromethoxy)phenoxy]benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC(Cl)=C(Cl)C=C1OC1=CC=C(OC(F)(F)F)C=C1 NJFDHBSKHZPRIL-UHFFFAOYSA-N 0.000 claims 1
- JXVMPMSRFGGAGY-UHFFFAOYSA-N 4-chloro-3-[(2-phenoxybenzoyl)amino]benzoic acid Chemical compound ClC1=C(C=C(C(=O)O)C=C1)NC(C1=C(C=CC=C1)OC1=CC=CC=C1)=O JXVMPMSRFGGAGY-UHFFFAOYSA-N 0.000 claims 1
- WRZOPENWRAIPLT-UHFFFAOYSA-N 4-methyl-3-[(2-phenoxybenzoyl)amino]benzoic acid Chemical compound CC1=C(C=C(C(=O)O)C=C1)NC(C1=C(C=CC=C1)OC1=CC=CC=C1)=O WRZOPENWRAIPLT-UHFFFAOYSA-N 0.000 claims 1
- SEAWCQYTEVZJDD-UHFFFAOYSA-N 5-[(4,5-dichloro-2-phenoxybenzoyl)amino]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1NC(=O)C1=CC(Cl)=C(Cl)C=C1OC1=CC=CC=C1 SEAWCQYTEVZJDD-UHFFFAOYSA-N 0.000 claims 1
- JFTGNYZRKUMSAG-UHFFFAOYSA-N 5-[[2-(2,4-dimethoxyphenoxy)-4,6-bis(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound COC1=CC(OC)=CC=C1OC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1C(=O)NC1=CC=C(C(O)=O)N=C1 JFTGNYZRKUMSAG-UHFFFAOYSA-N 0.000 claims 1
- NOKQAGXWKAATRB-UHFFFAOYSA-N 5-[[2-(2,4-dimethoxyphenoxy)-5-(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound COC1=CC(OC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC=C(C(O)=O)N=C1 NOKQAGXWKAATRB-UHFFFAOYSA-N 0.000 claims 1
- ZJDFLPLEPVWDIP-UHFFFAOYSA-N 5-[[2-(2-chloro-4-fluorophenoxy)-5-(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1NC(=O)C1=CC(C(F)(F)F)=CC=C1OC1=CC=C(F)C=C1Cl ZJDFLPLEPVWDIP-UHFFFAOYSA-N 0.000 claims 1
- KTHRLYGNINDXBX-UHFFFAOYSA-N 5-[[2-(2-chloro-4-fluorophenoxy)-6-(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1NC(=O)C(C(=CC=C1)C(F)(F)F)=C1OC1=CC=C(F)C=C1Cl KTHRLYGNINDXBX-UHFFFAOYSA-N 0.000 claims 1
- HKWSUHGMFVMEIM-UHFFFAOYSA-N 5-[[2-(2-chloro-4-methoxyphenoxy)-5-(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound ClC1=CC(OC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC=C(C(O)=O)N=C1 HKWSUHGMFVMEIM-UHFFFAOYSA-N 0.000 claims 1
- QOJHXRSRBOSGMJ-UHFFFAOYSA-N 5-[[2-(2-methoxyphenoxy)-4,6-bis(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound COC1=CC=CC=C1OC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1C(=O)NC1=CC=C(C(O)=O)N=C1 QOJHXRSRBOSGMJ-UHFFFAOYSA-N 0.000 claims 1
- BQNMADFVJFWVJU-UHFFFAOYSA-N 5-[[2-(2-methoxyphenoxy)-5-(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound COC1=CC=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC=C(C(O)=O)N=C1 BQNMADFVJFWVJU-UHFFFAOYSA-N 0.000 claims 1
- SCVAJTQTAYTWBF-UHFFFAOYSA-N 5-[[2-(2-propan-2-yloxyphenoxy)-5-(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound CC(C)OC1=CC=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC=C(C(O)=O)N=C1 SCVAJTQTAYTWBF-UHFFFAOYSA-N 0.000 claims 1
- BIRRZQIINJYINB-UHFFFAOYSA-N 5-[[2-(3-fluoro-2-methoxyphenoxy)-5-(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound COC1=C(F)C=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC=C(C(O)=O)N=C1 BIRRZQIINJYINB-UHFFFAOYSA-N 0.000 claims 1
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- RRSGOCVSLFHGAX-UHFFFAOYSA-N 5-[[2-(4-chloro-2-methylphenoxy)-5-(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound CC1=CC(Cl)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC=C(C(O)=O)N=C1 RRSGOCVSLFHGAX-UHFFFAOYSA-N 0.000 claims 1
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| US2511231A (en) * | 1949-03-26 | 1950-06-13 | Eastman Kodak Co | 1-cyanophenyl-3-acylamino-5-pyrazolone couplers for color photography |
| KR20080109918A (ko) | 2006-04-11 | 2008-12-17 | 버텍스 파마슈티칼스 인코포레이티드 | 전압 개폐 나트륨 채널의 억제제로서 유용한 조성물 |
| MX2010003865A (es) | 2007-10-11 | 2010-06-01 | Vertex Pharma | Aril amidas utiles como inhibidores de canales de sodio dependientes de voltaje. |
| RU2010118481A (ru) * | 2007-10-11 | 2011-11-20 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | Амиды, применимые в качестве ингибиторов потенциалзависимых натриевых каналов |
| NZ584475A (en) | 2007-10-11 | 2012-07-27 | Vertex Pharma | Heteroaryl amides useful as inhibitors of voltage-gated sodium channels |
| JP5685203B2 (ja) * | 2009-05-29 | 2015-03-18 | ラクオリア創薬株式会社 | カルシウムチャネル遮断薬またはナトリウムチャネル遮断薬としてのアリール置換カルボキサミド誘導体 |
-
2014
- 2014-01-29 AU AU2014212431A patent/AU2014212431B2/en active Active
- 2014-01-29 MX MX2015009591A patent/MX359882B/es active IP Right Grant
- 2014-01-29 US US14/167,741 patent/US9108903B2/en active Active
- 2014-01-29 SG SG11201505954RA patent/SG11201505954RA/en unknown
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- 2014-01-29 BR BR112015018284-4A patent/BR112015018284B1/pt not_active IP Right Cessation
- 2014-01-29 CN CN201480006878.4A patent/CN104968647B/zh active Active
- 2014-01-29 AR ARP140100282A patent/AR094668A1/es unknown
- 2014-01-29 RU RU2015136779A patent/RU2658920C2/ru active
- 2014-01-29 CA CA2898653A patent/CA2898653C/en active Active
- 2014-01-29 KR KR1020157023600A patent/KR102226588B1/ko not_active Expired - Fee Related
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- 2014-01-29 JP JP2015556113A patent/JP6346622B2/ja active Active
- 2014-01-29 WO PCT/US2014/013667 patent/WO2014120820A1/en not_active Ceased
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